NHL playoffs bracket 2019: Western Conference series picks, breakdowns, Stanley Cup predictions It’s now time for the greatest postseason tournament in all of professional sports — the NHL’s Stanley Cup playoffs. While we all start off thinking one team is a sure-fire pick to win it all, one bounce or post or bad bounce can alter a team’s destiny. Can Calgary put up similar numbers in the postseason or was their best years 1989 — the year it won it’s last Cup — a fluke? Will they, or Winnipeg, become the first Canadian team win since Montreal in 1993 or will the Blues derail their dreams and keep their own Cinderella season going? How it will all end is anyone’s guess, but Sporting News’ NHL experts still tried to predict the Western Conference playoffs and who will take a lap with Lord Stanley’s Cup in June.